JP2021513516A - Compounds for organic electronic devices, organic electronic devices using them, and their electronic devices - Google Patents

Abstract

The present invention provides a novel compound capable of improving the luminous efficiency, stability and life of the device, an organic electronic device using the same, and an electronic device thereof.

Description

The present invention relates to a compound for an organic electronic device, an organic electronic device using the compound, and an electronic device thereof.

In general, the organic light emission phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic substance. An organic electronic device utilizing an organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic substance layer between them. Here, in order to enhance the efficiency and stability of the organic electronic device, the organic substance layer often has a multi-layered structure composed of different substances, for example, a hole injection layer, a hole transport layer, and a light emitting layer. , An electron transport layer, an electron injection layer, and the like.

In an organic electronic device, a material used as an organic material layer can be classified into a light emitting material and a charge transporting material, for example, a hole injecting material, a hole transporting material, an electron transporting material, an electron injecting material, and the like.

Further, the luminescent material is classified into a high molecular weight type and a low molecular weight type according to the molecular weight, and a fluorescent material derived from the singlet excited state of electrons and a phosphorescent material derived from the triplet excited state of electrons according to the light emitting mechanism. Can be classified as. In addition, the luminescent material can be classified into blue, green, red luminescent materials and yellow and orange luminescent materials necessary for achieving a better natural color, depending on the luminescent color.

On the other hand, when only one substance is used as the light emitting material, there is a problem that the maximum light emitting wavelength moves to a long wavelength due to the interaction between molecules and the color purity is lowered, or the efficiency of the device is lowered due to the light emitting reducing effect. Since it is generated, a host / dopant system can be used as the light emitting material in order to increase the color purity and improve the luminous efficiency through energy transfer. The principle is that if a small amount of a dopant having a smaller energy bandwidth than the host forming the light emitting layer is mixed with the light emitting layer, excitons generated from the light emitting layer are transported to the dopant to emit highly efficient light. At this time, since the wavelength of the host moves to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

The current portable display market tends to grow in size to large area displays, which requires greater power consumption than traditional portable displays. .. Therefore, from the standpoint of portable displays, which have a limited power source of batteries, power consumption is a very important factor, and efficiency and longevity issues must also be resolved. is there.

Efficiency, life, drive voltage, etc. are interrelated, and as efficiency increases, the drive voltage becomes relatively low, and when the drive voltage decreases, crystallization of organic substances due to Joule heat generated during drive decreases, resulting in It shows a tendency to extend the life. However, even if the organic layer is simply improved, the efficiency cannot be maximized. This is because long life and high efficiency can be achieved at the same time when the optimum combination of energy level and T1 value between organic substances, unique properties of substances (mobility, interface properties, etc.) is achieved. Is. Therefore, it is necessary to develop a light emitting material having high thermal stability and capable of efficiently establishing charge balance in the light emitting layer.

That is, in order to fully exhibit the excellent characteristics of the organic electronic device, the substances constituting the organic substance layer in the device, for example, a hole injecting substance, a hole transporting substance, a luminescent substance, an electron transporting substance, and an electron injecting substance , The light emitting auxiliary layer material must be supported by a stable and efficient material, but the development of a stable and efficient organic layer material for organic electronic devices has not yet progressed sufficiently. Is. Therefore, the development of new materials is required, and in particular, the development of the host material of the light emitting layer is urgently required.

On the other hand, in the case of a ring compound containing a hetero atom, the difference in properties depending on the material structure is very large, and it is applied to various layers as an OLED material. In particular, the band gap (HOMO, LUMO), electrical properties, chemical properties, physical properties, etc. differ depending on the number and condensation positions of the rings, the type and arrangement of heteroatoms, and so on. Application development has been promoted for various OLEDL layers. Recently, OLED materials for the types, numbers, and positions of heteroatoms of ring compounds have been actively developed.

Patent Document 1 was referred to as a prior document.

US Patent US 8334058 B2

The present invention is a compound capable of maximizing the effect of improving luminous efficiency and long life while maintaining the driving voltage of the device or slightly lowering it by utilizing the characteristics of the ring compound, and organic electrons using the compound. It is an object of the present invention to provide an element and an electronic device thereof.

The present invention provides a compound represented by the following formulas (1) and (18), an organic electronic device containing the same, and an electronic device thereof:

By using the compound according to the present invention, high luminous efficiency, low drive voltage, and high heat resistance of the device can be achieved, and the color purity and life of the device can be greatly improved.

It is an example figure of the organic electron light emitting device which concerns on this invention.

Hereinafter, a detailed description will be given with reference to examples of the present invention. In the description of the present invention, if it is determined that a specific description of the related known configuration or function may obscure the gist of the present invention, the detailed description thereof will be omitted.

In addition, terms such as first, second, A, B, (a), and (b) can be used in the description of the components of the present invention. Such a term is for distinguishing a component from other components, and the term does not limit the essence, order, or order of the component. If a component is described as being "connected," "joined," or "connected" to another component, that component is directly connected or connected to the other component. However, it should be understood that other components may also be "tied", "joined" or "connected" between components.

As used herein and in the appended claims, unless otherwise stated, the following terms have the following meanings.

As used herein, the term "halo" or "halogen" is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I), unless otherwise stated.

Unless otherwise specified, the term "alkyl" or "alkyl group" used in the present invention has a single bond having 1 to 60 carbon atoms, and is a linear alkyl group, a branched alkyl group, or a cycloalkyl. It means a radical of a saturated aliphatic functional group including a (aliphatic group) group, an alkyl-substituted cycloalkyl group, and a cycloalkyl-substituted alkyl group.

As used in the present invention, the term "haloalkyl group" or "halogenalkyl group" means an alkyl group substituted with halogen unless otherwise specified.

The term "heteroalkyl group" used in the present invention means that one or more of the carbon atoms constituting the alkyl group are replaced by a heteroatom.

Unless otherwise specified, the terms "alkenyl group", "alkenyl group" or "alkynyl group" used in the present invention each have a double or triple bond having 2 to 60 carbon atoms and are linear. It includes, but is not limited to, a shaped or branched chain group.

The term "cycloalkyl" as used in the present invention means, but is not limited to, an alkyl forming a ring having 3 to 60 carbon atoms, unless otherwise specified.

The terms "alkoxyl group", "alkoxy group" or "alkyloxy group" used in the present invention mean an alkyl group to which an oxygen radical is attached, and have 1 to 60 carbon atoms unless otherwise specified. Has, and is not limited to this.

The terms "alkeneoxyl group", "alkeneoxy group", "alkenyloxyl group", or "alkenyloxy group" used in the present invention mean an alkenyl group to which an oxygen radical is attached, and there is no particular explanation. As long as it has 2 to 60 carbon atoms, it is not limited to this.

The term "aryloxyl group" or "aryloxy group" used in the present invention means an aryl group to which an oxygen radical is attached and has 6 to 60 carbon atoms unless otherwise specified. It is not limited to.

Unless otherwise specified, the terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms and are not limited thereto. In the present invention, an aryl group or an arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by adjoining substituents participating in a bond or reaction. For example, the aryl group may be a phenyl group, a biphenyl group, a fluorene group, or a spirofluorene group.

The prefix "aryl" or "earl" means a radical substituted with an aryl group. For example, an arylalkyl group is an alkyl group substituted with an aryl group, an arylalkenyl group is an alkenyl group substituted with an aryl group, and a radical substituted with an aryl group is a carbon described herein. Have a number.

Also, when the prefixes are named consecutively, it means that the substituents are listed in the order described above. For example, in the case of an arylalkoxy group, it means an alkoxy group substituted with an aryl group, in the case of an alkoxylcarbonyl group, it means a carbonyl group substituted with an alkoxyl group, and in the case of an arylcarbonylalkenyl group, it means an arylcarbonyl. It means an alkoxy group substituted with a group, where the arylcarbonyl group is a carbonyl group substituted with an aryl group.

As used herein, the term "heteroalkyl" means an alkyl containing one or more heteroatoms, unless otherwise stated. As used in the present invention, the terms "heteroaryl group" or "heteroarylene group" mean aryl or arylene groups having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. , But not limited to this, it may contain at least one of a monocyclic ring and a polycyclic ring, and may be formed by bonding adjacent functional groups.

Unless otherwise specified, the term "heterocyclic group" used in the present invention contains one or more heteroatoms, has 2 to 60 carbon atoms, and is at least one of a monocyclic ring and a polycyclic ring. Includes a heteroaliphatic ring and a heteroaromatic ring. Adjacent functional groups may be bonded to form.

As used herein, the term "heteroatom" refers to N, O, S, P or Si, unless otherwise stated.

The "heterocyclic group" may also include a ring containing _{SO 2} instead of the carbon to be formed. For example, the "heterocyclic group" includes the following compounds.

Unless otherwise specified, the term "aliphatic" used in the present invention means an aliphatic hydrocarbon having 1 to 60 carbon atoms, and "aliphatic ring" means an aliphatic hydrocarbon having 3 to 60 carbon atoms. It means a hydrogen ring.

Unless otherwise stated, the term "ring" used in the present invention refers to an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocycle having 2 to 60 carbon atoms, or a heterocycle thereof. It means a fused ring consisting of a combination, and includes a saturated or unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentioned hetero compounds may contain, and are not limited to, one or more hetero atoms.

Unless otherwise specified, the term "carbonyl" used in the present invention is indicated by -COR', where R'is hydrogen, an alkyl group having 1 to 20 carbon atoms, and 6 carbon atoms. It is an aryl group having ~ 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.

Unless otherwise specified, the term "ether" used in the present invention is represented by -R-OR', where R or R'are independent of hydrogen and carbon, respectively. An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof. is there.

Further, unless otherwise described, "substituted" in the terms used "substituted or unsubstituted" in the present invention, deuterium, halogen, amino group, nitrile group, a nitro group, a C ₁ -C ₂₀ alkyl _group, an alkoxyl group of _{C 1 -C 20, C 1 -C} 20 alkyl amine _group, an alkyl thiophene group of C 1 _{-C 20,} aryl thiophene group of C 6 _{-C 20,} alkenyl groups C 2 _{-C 20} , an alkynyl group of _C 2 _{-C 20,} cycloalkyl group of C 3 _{-C 20,} aryl group of C 6 _{-C 20,} aryl group of _C 6 _{-C 20} substituted with _deuterium, a C 8 _{-C 20} means an arylalkenyl group, a silane group, a boron group, those substituted with one or more substituents selected from the group consisting of heterocyclic groups germanium group and C ₂ -C _20, it is limited to substituents It's not a thing.

（式中、ａが０の整数である場合、置換基Ｒ^１は存在しなく、ａが１の整数である場合、１つの置換基Ｒ^１は、ベンゼン環を形成する炭素のうちの何れか１つの炭素に結合し、ａが２又は３の整数である場合、それぞれ下記のように結合し、このとき、Ｒ^１は互いに同一又は異なってもよく、ａが４〜６の整数である場合、これと類似する方式でベンゼン環の炭素に結合し、一方、ベンゼン環を形成する炭素に結合されている水素の表示は省略する。）

Further, unless otherwise specified, the formula used in the present invention is applied in the same manner as the definition of the substituent by the definition of the exponent in the following formula.

(Wherein, when a is an integer of 0, the substituents R ¹ is not present and when a is the integer 1, one substituent R ¹ is any of the carbons constituting the benzene ring When it is bonded to one carbon and a is an integer of 2 or 3, they are bonded as ^{follows. At this time, R 1} may be the same or different from each other, and when a is an integer of 4 to 6. , The indication of hydrogen bonded to the carbon of the benzene ring by a method similar to this, while being bonded to the carbon forming the benzene ring is omitted.)

Hereinafter, the compound according to one aspect of the present invention and the organic electronic device containing the compound will be described.

［式中、１）Ａｒ^１、Ａｒ^２及びＡｒ^３は、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基であり、
２）ｌ＋ｅは０〜４の整数、ｄ＋ｍは０〜４の整数、ａ及びｂは０〜３の整数、ｎは１〜３の整数、ｃは０〜４の整数であり、
３）Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４及びＲ^５は、互いに独立して、水素；重水素；ハロゲン；Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）｛ここで、Ｌ’は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、Ｒ_ａ及びＲ_ｂは、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれる｝；からなる群から選ばれ、又は複数のＲ^１同士、複数のＲ^２同士、複数のＲ^３同士、複数のＲ^４同士、複数のＲ^５同士は、互いに結合して、芳香族及びヘテロ芳香環を形成していてもよく、
前記アリール基、フルオレニル基、アリーレン基、ヘテロ環基、フルオレニレン基、縮合環基、アルキル基、アルケニル基、アルコキシ基及びアリールオキシ基はそれぞれ重水素；ハロゲン；シラン基；シロキサン基；ホウ素基；ゲルマニウム基；シアノ基；ニトロ基；Ｃ_１−Ｃ_２０のアルキルチオ基；Ｃ_１−Ｃ_２０のアルコキシル基；Ｃ_１−Ｃ_２０のアルキル基；Ｃ_２−Ｃ_２０のアルケニル基；Ｃ_２−Ｃ_２０のアルキニル基；Ｃ_６−Ｃ_２０のアリール基；重水素で置換されたＣ_６−Ｃ_２０のアリール基；フルオレニル基；Ｃ_２−Ｃ_２０のヘテロ環基；Ｃ_３−Ｃ_２０のシクロアルキル基；Ｃ_７−Ｃ_２０のアリールアルキル基及びＣ_８−Ｃ_２０のアリールアルケニル基；からなる群から選ばれた一つ以上の置換基でさらに置換されていてもよくて、また、これらの置換基は、互いに結合して、環を形成していてもよく、ここで、「環」は、Ｃ_３−Ｃ_６０の脂肪族環又はＣ_６−Ｃ_６０の芳香族環又はＣ_２−Ｃ_６０のヘテロ環又はこれらの組み合わせからなる縮合環を意味し、飽和又は不飽和環を含む。］ The present invention provides a compound represented by the following formula (1):

[In the formula, 1) Ar ¹ , Ar ² and Ar ³ are aryl groups of _{C 6 to} C ₆₀ independently of each other.
2) l + e is an integer of 0 to 4, d + m is an integer of 0 to 4, a and b are integers of 0 to 3, n is an integer of 1 to 3, and c is an integer of 0 to 4.
3) R ¹ , R ² , R ³ , R ⁴ and R ⁵ are independent of each other, hydrogen; heavy hydrogen; halogen; _{aryl groups of C 6 to} C ₆₀ ; fluorenyl groups; O, N, S, Si and _{Heteroatoms of C 2 to} C ₆₀ containing at least one heteroatom of P; fused ring groups of the aliphatic rings of C _{3 to} C _{60 and the aromatic rings of C 6 to} C _{60 ; of C 1 to} C ₅₀ . an aryloxy group having C 6 _{-C 30;;} alkyl _group; a C 2 _{-C 20} alkynyl _group;; C 2 _{-C 20} alkenyl group C 1 _{-C 30} alkoxyl group and -L'-N _(R a) _(R b) {wherein, L 'represents a single _bond; fused ring with C 3 aliphatic ring and _C 6 _{-C 60} of _{-C 60} aromatic _ring; C for 6 _{-C 60} arylene group; fluorenylene group selected from the group consisting of, _{R a} and _{R b} are, independently of one _another, a C 6 _{-C 60} aryl group; a heterocyclic group and _C 2 _{-C 60;} group C 3 _{-C 60;} fluorenyl group A group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C _{6 to} C ₆₀ ; and a hetero ring group of _{C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; } selected from; selected from the group consisting of, or a plurality of R ¹ each other, a plurality of R ² to each other, a plurality of R ³ to each other, a plurality of R ⁴ with each other, a plurality of R ⁵ each other, bonded to each other, an aromatic May form group and heteroaromatic rings,
The aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each heavy hydrogen; halogen; silane group; siloxane group; boron group; germanium. Groups; Cyano groups; Nitro groups; C _1- C ₂₀ alkylthio groups; C _1- C ₂₀ alkoxyl groups; C _1- C ₂₀ alkyl groups; C _2- C ₂₀ alkenyl groups; C _2- C ₂₀ cycloalkyl groups C 3 _{-C 20;} heterocyclic group of C 2 _{-C 20;} alkynyl _group; C 6 _{-C 20} aryl group; a _C 6 _{-C 20} substituted with deuterium aryl group; a fluorenyl group; It may be further substituted with one or more substituents selected from the group consisting of _{C 7-} C ₂₀ arylalkyl groups and C _8- C _{20 arylalkenyl groups; and these substituents may be.} , They may be combined with each other to form a ring, where the "ring" is an aliphatic ring of _{C 3-} C ₆₀ or an aromatic ring of _{C 6-} C ₆₀ or a hetero of _{C 2-} C _60. It means a fused ring composed of a ring or a combination thereof, and includes a saturated or unsaturated ring. ]

（式中、Ａｒ^１、Ａｒ^２、Ａｒ^３、ｌ、ｍ、ｎ、ａ、ｂ、ｃ、ｄ、ｅ、ｎ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４及びＲ^５は、前記記載の定義と同義である。） Specifically, in the present invention, the compound represented by the above formula (1) includes a compound represented by any one of the following formulas (2) to (7):

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are described above. Synonymous with definition.)

Preferably, at least one ^{of Ar 1} , Ar ³ and R ³ of the formula (1) contains a compound which is an aryl group of _{C 6 to} C ₂₄ ^{, and more preferably Ar 1} or Ar of the formula (1). ³ contains a compound which is an aryl group of C _{6 to} C _24.

Further, the present invention, ^{R 3} in the formula (1) provides a compound which is an aryl group of C6-C24.

（式中、Ａｒ^１、Ａｒ^２、Ａｒ^３、ｌ、ｍ、ｎ、ａ，ｂ、ｃ、ｄ、ｅ、ｎ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５は、前記記載の定義と同義である。） Further, in the present invention, the formula (1) includes a compound represented by any one of the following formulas (8) to (10):

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are described above. Synonymous with definition.)

（式中、Ａｒ^１、Ａｒ^２、Ａｒ^３、ｌ、ｍ、ｎ、ａ、ｂ、ｃ、ｄ、ｅ、ｎ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５は、前記記載の定義と同義である。） Further, in the present invention, the compound represented by the above formula (1) includes a compound represented by the following formula (11):

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ , and R ⁵ are described above. Synonymous with definition.)

Specifically, in the present invention, the compound represented by the formula (1) includes the following compounds P-1 to P-160:

In another aspect, the present invention includes a first electrode; a second electrode; and an organic layer formed between the first electrode and the second electrode and containing the compound represented by the formula (1). Provided is an organic electronic device.

The organic material layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and the hole injection layer and holes. At least one layer of the transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer contains one kind alone or two or more kinds of the compound of the above formula (1). Preferably, the compound is contained in the light emitting layer.

［式中、１）Ｚ^１〜Ｚ^１６は、それぞれ独立して、ＣＲ又はＮ（ここで、Ｒは、水素、Ｃ_６〜Ｃ_６０のアリール基；Ｏ、Ｎ、Ｓ、Ｓｉ、Ｐの少なくとも一つのヘテロ原子を含むＣ_３〜Ｃ_６０のヘテロ環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_６〜Ｃ_６０のアリールアミン基；フルオレン基；からなる群から選ばれ、隣接する基と結合して環を形成していてもよい）であり、
２）Ｌ^２は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；Ｃ_３〜Ｃ_６０のヘテロアリーレン基；及び２価の脂肪族炭化水素基；からなる群から選ばれる基であり、
３）Ｗは、ＮＡｒ^５、Ｏ、Ｓ又はＣＲ’Ｒ’’（ここで、Ｒ’及びＲ’’は、それぞれ独立して、Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_６〜Ｃ_６０のアリール基；又はＯ、Ｎ、Ｓ、Ｓｉ、Ｐの少なくとも一つのヘテロ原子を含むＣ_３〜Ｃ_６０のヘテロ環基であり、これらは、互いに結合して、スピロ化合物を形成していてもよい）であり、
４）Ａｒ^４及びＡｒ^５は、それぞれ独立して、Ｃ_６〜Ｃ_６０のアリール基；Ｏ、Ｎ、Ｓ、Ｓｉ、Ｐの少なくとも一つのヘテロ原子を含むＣ_３〜Ｃ_６０のヘテロ環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_６〜Ｃ_６０のアリールアミン基；フルオレン基；からなる群から選ばれる。］ More specifically, an organic electronic device further comprising a compound represented by the following formula (12) in the light emitting layer is provided:

[In the formula, 1) Z ^{1 to} Z ¹⁶ are independently CR or N (where R is hydrogen, _{an aryl group of C 6 to} C ₆₀ ; at least of O, N, S, Si and P). Selected from the group consisting of a heterocyclic group of _{C 3 to} C ₆₀ containing one heteroatom; an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C ₆₀ ; a fluorene group; and bonded to an adjacent group. To form a ring)
2) L ² is a group selected from the group consisting of a single bond; an arylene group of _{C 6 to} C _{60 ; a heteroarylene group of C 3 to} C ₆₀ ; and a divalent aliphatic hydrocarbon group;
3) W is ^{NAr 5} , O, S or CR'R'' (where R'and R'' are independently alkyl groups of _{C 1 to} C ₅₀ ; aryls of _{C 6 to} C _{60. Groups; or C 3 to} C ₆₀ heterocyclic groups containing at least one heteroatom of O, N, S, Si, P, which may be attached to each other to form a spiro compound). And
4) Ar ⁴ and Ar ⁵ are independent _{aryl groups of C 6 to} C ₆₀ ; heterocyclic groups of _{C 3 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; It is selected from the group consisting of an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C _{60; a fluorene group;} ]

（式中、Ａｒ^４、Ａｒ^５，Ｚ^１〜Ｚ^１６、L２、Ｒ’、Ｒ’’は、前記記載の定義と同義である。） The formula (12) includes a compound represented by any one of the following formulas (13) to (16):

(In the formula, Ar ⁴ , Ar ⁵ , Z ^{1 to} Z ¹⁶ , L2, R', R'' are synonymous with the definitions described above.)

^{Preferably, Ar 4} and Ar ⁵ of the above formula (12) all contain compounds represented by aryl groups of _{C 6 to} C _30.

［式中、Ａｒ^４、Ａｒ^５、Ｚ^１〜Ｚ^１６、Ｌ^２は、前記記載の定義と同義であり、
１）Ｌ^１は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；Ｃ_３〜Ｃ_６０のヘテロアリーレン基；及び２価の脂肪族炭化水素基；からなる群から選ばれ、
２）Ｙは、Ｏ、Ｓ又はＮＡｒ^５であり、
３）Ｒ^ａ及びＲ^ｂは、互いに独立して、水素；重水素；ハロゲン；Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）｛ここで、Ｌ’は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＣ_２〜Ｃ^６０のヘテロ環基；からなる群から選ばれ、Ｒ_ａ及びＲ_ｂは、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、又は複数のＲ^１同士、複数のＲ^２同士、複数のＲ^３同士、複数のＲ^４同士、複数のＲ^５同士は、互いに結合して、芳香族及びヘテロ芳香環を形成していてもよい｝；からなる群から選ばれ、又は複数のＲ^ａ同士、複数のＲ^ｂ同士が互いに結合して、芳香族及びヘテロ芳香環を形成していてもよく、
４）ｙは、０〜３の整数であり、ｚは０〜４の整数である。］ Further, the compound represented by the above formula (12) includes a compound represented by the following formula (17):

[In the formula, Ar ⁴ , Ar ⁵ , Z ^{1 to} Z ¹⁶ , L ² are synonymous with the definitions described above.
1) L ¹ is selected from the group consisting of a single bond; an arylene group of _{C 6 to} C _{60 ; a heteroarylene group of C 3 to} C ₆₀ ; and a divalent aliphatic hydrocarbon group;
2) Y is O, S or NAr ⁵ and
3) R ^a and R ^b contain at least one heteroatom of hydrogen; heavy hydrogen; halogen; _{aryl group of C 6 to} C ₆₀ ; fluorenyl group; O, N, S, Si and P independently of each other. of _{C 2 ~C 20; C 2 ~C} 60 heterocyclic _group, alkyl group of _{C 1 ~C 50; C 3 ~C} 60 fused ring group and an aromatic ring of the aliphatic ring and _C 6 _{-C 60} Alkenyl groups; alkynyl groups of _{C 2 to} C ₂₀ ; alkoxyl groups of _{C 1 to} C _{30 ; aryloxy groups of C 6 to} C ₃₀ ; and -L'-N ( _Ra ) (R _b ) {where L 'Is a single bond; _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C _{60 ; and C 2 to} C ⁶⁰ . Selected from the group consisting of heterocyclic groups; _Ra and R _b are independent of each other, aryl groups of _{C 6 to} C ₆₀ ; fluorenyl groups; aliphatic rings of _{C 3 to} C _{60 and C 6 to} C _{60. Selected from the group consisting of fused ring groups with aromatic rings; and C 2 to} C ₆₀ hetero ring groups containing at least one heteroatom of O, N, S, Si and P; or a plurality of R ^1s. each other, a plurality of R ² to each other, a plurality of R ³ to each other, a plurality of R ⁴ with each other, a plurality of R ⁵ together are linked to each other, an aromatic and may also} to form a heteroaromatic ring; the group consisting of It may be selected from, or a plurality of Ras and ^a plurality of R ^bs may be bonded to each other to form an aromatic and a heteroaromatic ring.
4) y is an integer of 0 to 3, and z is an integer of 0 to 4. ]

Specifically, in the present invention, the compound represented by the above formula (12) includes the following 4-1 to 4-52:

［式（１）及び式（１８）中、
１）Ａｒ^１、Ａｒ^２、Ａｒ^３、ｌ、ｍ、ｎ、ａ、ｂ、ｃ、ｄ、ｅ、ｎ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４及びＲ^５は、請求項１に記載の定義と同義であり、
２）Ａｒ^４及びＡｒ^５は、お互い独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）｛ここで、Ｌ’は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、Ｒ_ａ及びＲ_ｂは、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、又はＡｒ^４とＡｒ^５が、互いに結合して、環を形成していてもよい｝；からなる群から選ばれ、
３）Ａｒ^６は、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれるか、又は下記式（１−a）、（１−b）、（１−c）の少なくとも一つであり、

４）Ａｒ^９〜Ａｒ^１１は、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）；からなる群から選ばれ、
５）ｈ、ｉ及びｇは、０〜４の整数であり；ｊは、０〜３の整数であり；Ｒ^６〜Ｒ^９は、同じであるか又は異なり、互いに独立して、水素；重水素；ハロゲン；Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）；からなる群から選ばれ、
又は、Ｒ^６〜Ｒ^９は、ｇ、ｈ、ｉ、ｊが２以上のとき、それぞれ複数として、互いに同じであるか又は異なり、互いに結合して、環を形成し、
６）Ｌ^６は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環の縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、
７）Ｌ^５は、Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれる。］ In another example, the present invention is an organic electronic element including a positive electrode; a negative electrode; and an organic material layer formed between the positive electrode and the negative electrode; the organic material layer includes a light emitting layer, and the positive electrode and the light emitting layer. The hole transport layer or the luminescence auxiliary layer includes a hole transport layer formed between the positive electrode and the luminescence auxiliary layer formed between the positive electrode and the hole transport layer; Provided is an organic electronic element containing the compound represented by the following formula (1) in the light emitting layer.

[In equations (1) and (18),
1) Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are described in claim 1. Is synonymous with the definition of
2) Ar ⁴ and Ar ⁵ are independent of each other and are C _{6 to} C _{60 aryl groups; fluorenyl groups; C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C _{2 to} C ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b ) {where L'is a single bond; C A group consisting of an arylene group of _{6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and a hetero ring group of _{C 2 to} C _60; is selected from, _{R a} and _{R b} are, independently of one _another, an aryl group of C 6 _{-C 60;} condensation of aromatic ring of C 3 aliphatic ring and _C 6 _{-C 60} of _{-C 60;} fluorenyl group Selected from the group consisting of ring groups; and _{C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P ^{; or Ar 4} and Ar ⁵ bonded to each other. , May form a ring}; selected from the group consisting of
3) Ar ⁶ is selected from the group consisting of _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a heterocyclic group of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Or at least one of the following formulas (1-a), (1-b), (1-c),

4) Ar ^{9 to} Ar ¹¹ are independent of each other, _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a hetero of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C ₂ to C 20 Selected from the group consisting of ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b);
5) h, i and g are integers from 0 to 4; j is an integer from 0 to 3; R ^{6 to} R ⁹ are the same or different, independent of each other, hydrogen; heavy. Hydrogen; Halogen; _{Aryl group of C 6 to} C ₆₀ ; Fluolenyl group; Hetero ring group of _{C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Fat of _{C 3 to} C ₆₀ alkynyl group _C 2 ~C _20;; alkenyl C 2 _{-C 20;} alkyl radical of C 1 _{-C 50;} fused ring group of the aromatic ring of the group ring and _C 6 _{~C 60 C} 1 _{~C 30} Alkyloxy groups of C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b );
Alternatively, ^{when g, h, i, and j are 2 or more, R 6 to} R ⁹ are the same or different from each other as a plurality, and are combined with each other to form a ring.
6) L ⁶ is a single bond; _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, Selected from the group consisting of _{C 2 to} C ₆₀ heterocyclic groups containing at least one heteroatom of S, Si and P;
7) L ⁵ is _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, S, heterocyclic group _C 2 _{-C 60} containing at least one heteroatom Si and P; selected from the group consisting of. ]

The present invention also provides an organic electronic device in which the light emitting layer further contains at least one compound represented by the formula (12).

［式中、１）Ａｒ^６’は、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、２）Ａｒ^４、Ａｒ^５、Ａｒ^９〜Ａｒ^１１、ｈ、ｉ、ｇ、Ｌ^５、Ｌ^６、Ｒ^６〜Ｒ^９は、前記記載の定義と同義である。］ Further, in the present invention, the hole transport layer contains a compound represented by the following formula (19) or (20), and the light emitting auxiliary layer contains an organic electron containing a compound represented by the following formula (21) or (22). Providing elements:

Wherein, 1) Ar ^{6 _'is} an aryl group of C 6 _{-C 60;} heterocyclic group _C 2 _{-C 60} containing O, N, S, at least one of the heteroatoms Si and P; fluorenyl group; 2) Ar ⁴ , Ar ⁵ , Ar ^{9 to} Ar ¹¹ , h, i, g, L ⁵ , L ⁶ , and R ^{6 to} R ⁹ are synonymous with the definitions described above. ]

Specifically, in the present invention, the compound represented by the above formula (18) includes the compounds represented by the following compounds 13-1 to 13-79 and 2-1 to 2-76.

［式中、Ｒ^２０、Ｒ^２１、Ｒ^２２、Ｒ^２３、Ｒ^２４及びＲ^２５は、互いに独立して、水素；重水素；ハロゲン；Ｃ_６〜Ｃ_３０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_３０のヘテロ環基；Ｃ_３〜Ｃ_３０の脂肪族環とＣ_６〜Ｃ_３０の芳香族環との縮合環基；Ｃ_１〜Ｃ_３０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；及びＣ_６〜Ｃ_３０のアリールオキシ基；からなる群から選ばれ、又は複数のＲ^２０同士、複数のＲ^２２同士、複数のＲ^２３同士、複数のＲ^２４同士、複数のＲ^２５同士は、互いに結合して、芳香族及びヘテロ芳香環を形成していてもよく、
ｖは、０〜３のいずれか一つの整数であり、
ｕ、ｗ，ｘ及びｙは、それぞれ独立して、０〜４のいずれか一つの整数であり、
Ｚは０〜５のいずれか一つの整数であり、
Ｌ^２０及びＬ^２１は、それぞれ独立して、単結合；Ｃ_６〜Ｃ_３０のアリーレン基；Ｃ_３〜Ｃ_３０のヘテロアリーレン基；であり、
Ａｒ^２０は、Ｃ_６〜Ｃ_３０のアリール基；又はＣ_３〜Ｃ_３０のヘテロアリーレン基；であり、
Ｘ^２０は、Ｏ、Ｓ、ＮＲ’又はＣＲ’Ｒ’’｛ここで、Ｒ’及びＲ’’は、それぞれ独立して、Ｃ_１〜Ｃ_３０のアルキル基；Ｃ_６〜Ｃ_３０のアリール基；又はＯ、Ｎ、Ｓ、Ｓｉ、Ｐの少なくとも一つのヘテロ原子を含むＣ_３〜Ｃ_３０のヘテロ環基；であり、これらは、互いに結合して、スピロ化合物を形成していてもよい｝である。］ In yet another example, the present invention is an organic electronic device including a positive electrode; a negative electrode; and an organic material layer formed between the positive electrode and the negative electrode; the organic material layer includes a light emitting layer, and the positive electrode and the light emitting layer. The hole transport layer formed between the two, and a light emitting auxiliary layer or an electron blocking layer (EBL) formed between the positive electrode and the hole transport layer are included, and the light emitting auxiliary layer or the electron blocking layer is represented by the following formula (30). Provided are an organic electronic device containing the compound represented by:

[In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are independent of each other: hydrogen; heavy hydrogen; halogen; _{aryl groups of C 6 to} C ₃₀ ; fluorenyl groups; O, N. , S, Si and P heteroatoms of C _{2 to} C ₃₀ containing at least one heteroatom; fused ring groups of C _{3 to} C ₃₀ aliphatic rings and C _{6 to} C ₃₀ aromatic rings; C from the group consisting of; and aryloxy groups of _{C 6 ~C 30; C 1 ~C} 30 alkoxy _group; C 2 _{-C 20} alkynyl _group; C 2 _{-C 20} alkenyl _{group; 1} -C ₃₀ alkyl group chosen, or a plurality of ^{R 20} each other between a plurality of ^{R 22,} together a plurality of ^{R 23,} a plurality of ^{R 24} to each other, a plurality of ^{R 25} each other, bonded to each other to form an aromatic or heteroaromatic ring May be
v is an integer of any one of 0 to 3.
u, w, x and y are independently integers of any one of 0 to 4.
Z is an integer of any one of 0 to 5,
L ²⁰ and L ²¹ are independently single bonds; C _{6 to} C ₃₀ arylene groups; C _{3 to} C ₃₀ heteroarylene groups;
Ar ²⁰ is _{an aryl group of C 6 to} C ₃₀ ; or a heteroarylene group of C _{3 to} C ₃₀ ;
X ²⁰ is O, S, NR'or CR'R'' {where R'and R'' are independently alkyl groups of _{C 1 to} C ₃₀ ; aryl groups of _{C 6 to} C _30. ; or O, N, S, Si, heterocyclic group of C ₃ -C 3 ₀ containing at least one heteroatom P; is, they may be bonded to each other to form a spiro compound }. ]

（式中、Ｒ^２０、Ｒ^２１、Ｒ^２２、Ｒ^２３、Ｒ^２４、Ｒ^２５、Ｌ^２０、Ｌ^２１、Ａｒ^２０及びＸ^２０、ｕ、v、ｗ、ｘ、ｙ及びｚは、前記記載の定義と同義である。） In the present invention, the compound represented by the formula (30) is represented by any one of the following formulas (31) to (38).

(In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , L ²⁰ , L ²¹ , Ar ²⁰ and X ²⁰ , u, v, w, x, y and z are described above. Synonymous with definition.)

In the present invention, the compound represented by the formula (30) includes the following compounds:

As shown in FIG. 1, the organic electronic element 100 according to the present invention has the first electrode 120, the second electrode 180, and the formula (1) between the first electrode 120 and the second electrode 180 formed on the substrate 110. It is provided with an organic material layer containing the compound represented by 1). At this time, the first electrode 120 may be an anode (positive electrode) and the second electrode 180 may be a cathode (negative electrode). In the case of an inverter, the first electrode is the cathode and the second electrode is the cathode. It may be an anode.

The organic material layer includes a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, a light emitting auxiliary layer 151, an electron transport layer 160, and an electron injection layer 170 in this order on the first electrode 120. At this time, the remaining layers other than the light emitting layer 150 may not be formed. The hole blocking layer, the electron blocking layer, the light emission assisting layer 151, the electron transport assisting layer, the buffer layer 141 and the like may be further included, and the electron transporting layer 160 and the like may play the role of the hole blocking layer.

Further, although not shown, the organic electronic device according to the present invention can further include a protective layer formed on at least one surface of the first electrode and the second electrode, which is opposite to the organic substance layer.

On the other hand, even in the same core, the band gap, electrical characteristics, interfacial properties, etc. change depending on which substituent is bonded to which position. Therefore, the selection of the core and the sub-substitution bonded to the core are selected. The combination of bodies is also very important, and in particular, when the energy level and T1 value between each organic substance, the intrinsic properties of the substance (mobility, interface properties, etc.) are optimally combined, a long life and high efficiency can be achieved at the same time. Can be achieved.

The organic electron light emitting device according to an embodiment of the present invention can be manufactured by using a PVD (physical vapor deposition) method. For example, a metal or a conductive metal oxide or an alloy thereof is vapor-deposited on a substrate to form a positive electrode, on which a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer are formed. It can be produced by forming an organic material layer including 160 and an electron injection layer 170, and then depositing a substance used as a negative electrode on the organic material layer. Further, a light emitting auxiliary layer 151 can be further formed between the hole transport layer 140 and the light emitting layer 150, and an electron transport auxiliary layer can be further formed between the light emitting layer 150 and the electron transport layer 160.

As yet another specific example, the present invention provides an organic electronic device in which the light emitting layer is a phosphorescent light emitting layer in the organic material layer.

Further, in the present invention, in the light emitting layer of the organic substance layer, the compounds represented by the formulas (1) and (18) are mixed at any one ratio of 1: 9 to 9: 1 and contained in the light emitting layer. Provide an electronic element. Therefore, the compound represented by the formula (12) is further mixed to provide an organic electronic device contained in the light emitting layer.

According to the present invention, in the organic electronic device, at least one of one side surface of the first electrode and one side opposite to the organic material layer or one side surface of the second electrode and one side opposite to the organic material layer. Provided is an organic electronic device further including a light efficiency improving layer formed therein.

In yet another example, the present invention provides an organic electronic device in which the compound represented by the formula (30) is used in a light emitting auxiliary layer or an electron blocking layer, preferably contained in a green light emitting auxiliary layer. More specifically, it provides an organic electronic device in which the compound represented by the formula (39) or the formula (40) is contained in the green light emitting auxiliary layer.

Further, in the present invention, the organic substance layer is formed by any one of a spin coating step, a nozzle printing step, an inkjet printing step, a slot coating step, a dip coating step and a roll-to-roll step, and the organic matter according to the present invention. Since the layer can be formed by various methods, the forming method does not limit the scope of rights of the present invention.

The organic electronic device according to the embodiment of the present invention may be a front light emitting type, a back light emitting type, or a double-sided light emitting type depending on the material used.

WOLED (White Organic Light Emitting Device) is easy to realize high resolution and has excellent processability, but has an advantage that it can be manufactured by using the conventional LCD color filter technology. Mainly, various structures for white organic light emitting devices used in backlight devices have been proposed and patented. Typically, R (red), G (green), and B (blue) light emitting parts are arranged in parallel in parallel with each other (side-by-side) method, and R, G, and B light emitting layers are laminated one above the other. There is a (stacking) method, which is a color conversion material (CCM) method that utilizes electric field emission by a blue (B) organic light emitting layer and photoluminescence of an inorganic phosphor using light from these. However, the present invention can also be applied to such OLEDs.

The present invention also provides an electronic device including a display device including the organic electronic element described above; and a control unit for driving the display device;

In yet another aspect, the organic electronic device is at least one of an organic electron light emitting device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination element. Is provided in the present invention. At this time, the electronic device may be a current or future wireless communication terminal, such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation system, a game machine, various TVs, and various computers. Including all electronic devices.

Hereinafter, a synthesis example of the compound represented by the formula (1) of the present invention and a production example of the organic electronic device of the present invention will be specifically described with reference to Examples, but the following Examples of the present invention will be used. It is not limited.

[Synthesis Example 1]
The compound (final product 1) represented by the formula (1) according to the present invention may be produced by reacting Core and Sub as in the reaction scheme 1 below, but is not limited thereto.
<Reaction scheme 1>

Example of Core Synthesis The Core of Reaction Scheme 1 may be synthesized by the reaction route of Reaction Scheme 2 below, but is not limited thereto.
<Reaction scheme 2>

Synthesis of Inter-1 In a round bottom flask, 2,4,6-trichloro-1,3,5-triazine (50 g, 410.1 mmol), phenylboronic acid (83.2 g, 451.1 mmol), Pd (PPh _3). ) ₄ (14.2 g, 12.3 mmol), K ₂ CO ₃ (170 g, 1.2 mol), THF (1.3 L) and water (700 mL) were added, and the mixture was stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with dichloromethane ₄ , concentrated, and then the produced compound is recrystallized from a silica gel column to add 55 g of Inter 1 (yield:: 60%) obtained.

Synthesis of Core In a round bottom flask, Inter-1 (10 g, 47 mmol), dibenzo [b, d] furan-3-ylboronic acid (12 g, 51.9 mmol), Pd (PPh ₃ ) ₄ (1.6 g, 1. 4 mmol), K2CO3 (20 g, 141 mmol), THF (160 mL), water (80 mL) were added and stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with dichloromethane ₄ and concentrated, and then the produced compound is recrystallized from a silica gel column to obtain 5.7 g of Core 1 (yield). Rate: 53%) was obtained.

Examples of Core are as follows, but are not limited to these. In addition, Table 1 below shows the FD-MS (electric field desorption mass spectrometry) values of some compounds belonging to Core.

Sub example

Examples of Sub are as follows, but are not limited to these. In addition, Table 2 below shows the FD-MS values of some compounds belonging to Sub.

丸底フラスコに、Ｃｏｒｅ２（５ｇ、１４ｍｍｏｌ）、Ｓｕｂ１（４．６ｇ、１５．２ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４ｍｍｏｌ）、Ｋ_２ＣＯ_３（５．７ｇ、４１．３ｍｍｏｌ）、ＴＨＦ、水を添加し、９０℃で撹拌した。反応が完了すれば、ＣＨ_２Ｃｌ_２と水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された化合物をシリカゲルカラム及び再結晶して、Ｐ−４１を４．６ｇ（収率：５７％）得た。 Product synthesis example P-41 synthesis example

In a round bottom flask, Core 2 (5 g, 14 mmol), Sub 1 (4.6 g, 15.2 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (5.7 g, 41. 3 mmol), THF and water were added and stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with sulfonyl ₄ and concentrated, and then the produced compound is recrystallized from a silica gel column to obtain 4.6 g of P-41. (Yield: 57%) was obtained.

丸底フラスコに、Ｃｏｒｅ１（５ｇ、１４ｍｍｏｌ）、Sub９（５．８ｇ、１５．４ｍｍｏｌ）、Ｐｄ（ＰＰｈ３）４（０．５ｇ、０．４ｍｍｏｌ）、Ｋ２ＣＯ３（５．８ｇ、４１．９ｍｍｏｌ）、ＴＨＦ、水を添加して９０℃で撹拌した。反応が完了すればＣＨ２Ｃｌ２と水で抽出した後有機層をＭｇＳＯ４で乾燥して濃縮した後生成された化合物をシリカゲルカラム及び再結晶してＰ−９１を４．７ｇ（収率：５１％）得た。 Synthesis example of P-91

In a round bottom flask, Core1 (5 g, 14 mmol), Sub9 (5.8 g, 15.4 mmol), Pd (PPh3) 4 (0.5 g, 0.4 mmol), K2CO3 (5.8 g, 41.9 mmol), THF , Water was added and the mixture was stirred at 90 ° C. When the reaction is completed, after extracting with CH2Cl2 and water, the organic layer is dried with dichloromethane4 and concentrated, and then the produced compound is recrystallized from a silica gel column to obtain 4.7 g (yield: 51%) of P-91. It was.

丸底フラスコに、Ｃｏｒｅ１（５ｇ、１４ｍｍｏｌ）、Ｓｕｂ１６（５．８ｇ、１５．４ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４ｍｍｏｌ）、Ｋ_２ＣＯ_３（５．８ｇ、４１．９ｍｍｏｌ）、ＴＨＦ、水を添加し、９０℃で撹拌した。反応が完了すれば、ＣＨ_２Ｃｌ_２と水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された化合物をシリカゲルカラム及び再結晶して、Ｐ−１０６を５．８ｇ（収率：６３％）得た。 Synthesis example of P-106

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub16 (5.8 g, 15.4 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (5.8 g, 41. 9 mmol), THF and water were added and stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with dichloromethane ₄ and concentrated, and then the produced compound is recrystallized from a silica gel column to obtain 5.8 g of P-106. (Yield: 63%) was obtained.

丸底フラスコに、Ｃｏｒｅ１１（５ｇ、１４ｍｍｏｌ）、Ｓｕｂ２（５．８ｇ、１５．４ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４ｍｍｏｌ）、Ｋ_２ＣＯ_３（５．８ｇ、４１．９ｍｍｏｌ）、ＴＨＦ、水を添加し、９０℃で撹拌した。反応が完了すれば、ＣＨ_２Ｃｌ_２と水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された化合物をシリカゲルカラム及び再結晶して、Ｐ−１４６を４．７ｇ（収率：５１％）得た。 Synthesis example of P-146

In a round bottom flask, Core 11 (5 g, 14 mmol), Sub2 (5.8 g, 15.4 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (5.8 g, 41. 9 mmol), THF and water were added and stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with dichloromethane ₄ , concentrated, and then the produced compound is recrystallized from a silica gel column to obtain 4.7 g of P-146. (Yield: 51%) was obtained.

丸底フラスコに、Ｃｏｒｅ１（５ｇ、１４ｍｍｏｌ）、Ｓｕｂ６（５．９ｇ、１５．４ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．５ｇ、０．４ｍｍｏｌ）、Ｋ_２ＣＯ_３（５．８ｇ、４１．９ｍｍｏｌ）、ＴＨＦ、水を添加し、９０℃で撹拌した。反応が完了すれば、ＣＨ_２Ｃｌ_２と水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された化合物をシリカゲルカラム及び再結晶してＰ−４を６．１ｇ（収率：６６％）得た。 Synthesis example of P-4

In a round bottom flask, Core 1 (5 g, 14 mmol), Sub6 (5.9 g, 15.4 mmol), Pd (PPh ₃ ) ₄ (0.5 g, 0.4 mmol), K ₂ CO ₃ (5.8 g, 41. 9 mmol), THF and water were added and stirred at 90 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ₂ and water, the organic layer is dried with dichloromethane ₄ , concentrated, and then the produced compound is recrystallized from a silica gel column to give 6.1 g of P-4 (6.1 g of P-4). Yield: 66%) was obtained.

Table 3 below shows the FD-MS values of some compounds belonging to Products.

[Synthesis Example 2]
The compound (final products 2) represented by the formula (12) according to the present invention may be produced by reacting Sub3-1 and Sub3-2 as in the following reaction scheme 4, but is not limited thereto.
<Reaction scheme 4>

３−ブロモ−９−フェニル−９Ｈ−カルバゾール（６．４ｇ、２０ｍｍｏｌ）をＴＨＦに溶解させた後に、（９−（４，６−ジフェニル−１，３，５−トリアジン−２−イル）−９Ｈ−カルバゾール−３−イル）ボロン酸（８．８ｇ、２０ｍｍｏｌ）、Ｐｄ（ＰＰｈ_３）_４（０．０３当量）、Ｋ_２ＣＯ_３（３当量）、水を添加した後、撹拌還流させた。反応が完了すれば、エーテルと水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された有機物をシリカゲルカラム及び再結晶して、生成物を９．２ｇ（収率：７２％）得た。 Synthesis example of 4-1

After dissolving 3-bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol) in THF, (9- (4,6-diphenyl-1,3,5-triazine-2-yl) -9H - carbazol-3-yl) boronic acid _{(8.8g, 20mmol), Pd (} PPh 3) 4 (0.03 _eq), K 2 _CO 3 (3 eq), after addition of water, was stirred at reflux. When the reaction is completed, after extraction with ether and water, the organic layer is dried with sulfonyl ₄ and concentrated, and then the produced organic substance is recrystallized from a silica gel column to obtain 9.2 g of the product (yield:). 72%) obtained.

１０−ブロモ−７−（ピリジン−２−イル）−７Ｈ−ベンゾ［ｃ］カルバゾール（７．５ｇ、２０ｍｍｏｌ）、ジベンゾ［ｂ，ｄ］フラン−２−イルボロン酸（４．２ｇ、２０ｍｍｏｌ）を、前記４−１合成方法と同様にして、生成物を６．５ｇ（収率：７１％）得た。 Synthesis example of 4-21

10-Bromo-7- (pyridin-2-yl) -7H-benzo [c] carbazole (7.5 g, 20 mmol), dibenzo [b, d] furan-2-ylboronic acid (4.2 g, 20 mmol), 6.5 g (yield: 71%) of the product was obtained in the same manner as in the 4-1 synthesis method.

９−（［１，１’−ビフェニル］−４−イル）−３−ブロモ−９Ｈ−カルバゾール（８．０ｇ、２０ｍｍｏｌ）、（９−（ナフタレン−２−イル）−９Ｈ−カルバゾール−３−イル）ボロン酸（６．７ｇ、２０ｍｍｏｌ）を、前記４−１合成方法と同様にして、生成物を９．２ｇ（収率：７５％）得た。 4-25 synthesis example

9-([1,1'-biphenyl] -4-yl) -3-bromo-9H-carbazole (8.0 g, 20 mmol), (9- (naphthalene-2-yl) -9H-carbazole-3-yl) ) Boronic acid (6.7 g, 20 mmol) was obtained in the same manner as in the above 4-1 synthesis method to obtain 9.2 g (yield: 75%) of the product.

３’−ブロモ−９−フェニル−９Ｈ−２，９’−ビカルバゾール（９．７ｇ、２０ｍｍｏｌ）、（９−フェニル−９Ｈ−カルバゾール−３−イル）ボロン酸（５．７ｇ、２０ｍｍｏｌ）を前記４−１合成方法と同様にして、生成物を９．５ｇ（収率：７３％）得た。 Synthesis example of 4-31

3'-Bromo-9-phenyl-9H-2,9'-bicarbazole (9.7 g, 20 mmol), (9-phenyl-9H-carbazole-3-yl) boronic acid (5.7 g, 20 mmol) above. 9.5 g (yield: 73%) of product was obtained in the same manner as in the 4-1 synthesis method.

３−ブロモ−９−（ジベンゾ［ｂ，ｄ］フラン−２−イル）−９Ｈ−カルバゾール（８．２ｇ、２０ｍｍｏｌ）、（１２−（［１，１’：４’，１’’−テルフェニル］−４−イル）−１２Ｈ−ベンゾ［４，５］チエノ［２，３−ａ］カルバゾール−３−イル）ボロン酸（１０．９ｇ、２０ｍｍｏｌ）を、前記４−１合成方法と同様にして、生成物を１１．５ｇ（収率：６９％）得た。 4-32 synthesis example

3-Bromo-9- (dibenzo [b, d] furan-2-yl) -9H-carbazole (8.2 g, 20 mmol), (12-([1,1': 4', 1''-terphenyl) ] -4-yl) -12H-benzo [4,5] thieno [2,3-a] carbazole-3-yl) boronic acid (10.9 g, 20 mmol) in the same manner as in the 4-1 synthesis method. , The product was obtained in an amount of 11.5 g (yield: 69%).

４−ブロモ−９−フェニル−９Ｈ−カルバゾール（６．４ｇ、２０ｍｍｏｌ）、（４−（ジベンゾ［ｂ，ｄ］チオフェン−３−イル）フェニル）ボロン酸（６．１ｇ、２０ｍｍｏｌ）を、前記４−１合成方法と同様にして、生成物を６．７ｇ（収率：６７％）得た。 Synthesis example of 4-34

4-Bromo-9-phenyl-9H-carbazole (6.4 g, 20 mmol), (4- (dibenzo [b, d] thiophene-3-yl) phenyl) boronic acid (6.1 g, 20 mmol), 4 above. -1 As in the synthesis method, 6.7 g (yield: 67%) of product was obtained.

３−ブロモ−９−フェニル−９Ｈ−カルバゾール（６．４ｇ、２０ｍｍｏｌ）、９（９，９−ジメチル−９Ｈ−フルオレン−３−イル）ボロン酸（４．８ｇ、２０ｍｍｏｌ）を、前記４−１合成方法と同様にして、生成物を６．１ｇ（収率：７０％）得た。 Synthesis example of 4-35

3-Bromo-9-Phenyl-9H-carbazole (6.4 g, 20 mmol), 9 (9,9-dimethyl-9H-fluorene-3-yl) boronic acid (4.8 g, 20 mmol), 4-1. The product was obtained in the same manner as in the synthesis method in an amount of 6.1 g (yield: 70%).

[Synthesis Example 3]
The compound (final products) represented by the formula (18) according to the present invention is produced by reacting as follows, but is not limited thereto.

９−（４’−ブロモ−［１，１’−ビフェニル］−４−イル）−９Ｈ−カルバゾール（９．６ｇ、２４ｍｍｏｌ）をトルエンに溶解させた後に、ジ（［１，１’−ビフェニル］−４−イル）アミン（６．４ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．０５当量）、ＰＰｈ_３（０．１当量）、ＮａＯｔ−Ｂｕ（３当量）をそれぞれ添加した後、１００℃で２４時間撹拌還流した。反応が終了すれば、エーテルと水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された有機物をシリカゲルカラム及び再結晶して、最終化合物１２．９ｇ（収率：８４％）を得た。 13-17 synthesis example

After dissolving 9- (4'-bromo- [1,1'-biphenyl] -4-yl) -9H-carbazole (9.6 g, 24 mmol) in toluene, di ([1,1'-biphenyl] After adding -4-yl) amine (6.4 g, 20 mmol), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaOt-Bu (3 equivalent), 100 The mixture was stirred and refluxed at ° C. for 24 hours. When the reaction is completed, the mixture is extracted with ether and water, the organic layer is dried on director ₄ , concentrated, and the produced organic substance is recrystallized from a silica gel column to obtain 12.9 g of the final compound (yield: 84). %) Was obtained.

３−（４−ブロモフェニル）−９−フェニル−９Ｈ−カルバゾール（９．６ｇ、２４ｍｍｏｌ）をトルエンに溶解させた後、Ｎ−（［１，１’−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（７．２ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．０５当量）、ＰＰｈ_３（０．１当量）、ＮａＯｔ−Ｂｕ（３当量）をそれぞれ添加した後、１００℃で２４時間撹拌還流した。反応が終了すれば、エーテルと水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された有機物をシリカゲルカラム及び再結晶して、最終化合物１３．８ｇ（収率：８５％）を得た。 13-32 synthesis example

After dissolving 3- (4-bromophenyl) -9-phenyl-9H-carbazole (9.6 g, 24 mmol) in toluene, N- ([1,1'-biphenyl] -4-yl) -9, 9-Dimethyl-9H-fluorene-2-amine (7.2 g, 20 mmol), Pd ₂ (dba) ₃ (0.05 equivalent), PPh ₃ (0.1 equivalent), NaOt-Bu (3 equivalent), respectively. After the addition, the mixture was stirred and refluxed at 100 ° C. for 24 hours. When the reaction is completed, the mixture is extracted with ether and water, the organic layer is dried on director ₄ and concentrated, and then the produced organic substance is recrystallized from a silica gel column to obtain 13.8 g of the final compound (yield: 85). %) Was obtained.

丸底フラスコに、Ｓｕｂ４（１９）（９．５ｇ、２０ｍｍｏｌ）、Ｓｕｂ５（４）（４．７ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、１００℃で反応を進めた。反応が完了すれば、ＣＨ_２Ｃｌ^２と水で抽出した後、有機層をＭｇＳＯ_４で乾燥し、濃縮した後、生成された有機物をシリカゲルカラム及び再結晶して、２−３４を９．８ｇ（収率：７８％）得た。 2-34 synthesis example

Sub4 (19) (9.5 g, 20 mmol), Sub5 (4) (4.7 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) in a round bottom flask. ) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol) and toluene (300 mL) were added, and then the reaction was proceeded at 100 ° C. When the reaction is completed _{, after extraction with CH 2} Cl ² and water, the organic layer is dried with dichloromethane ₄ , concentrated, and then the produced organic substance is recrystallized from a silica gel column to add 9.8 g of 2-34. (Yield: 78%) was obtained.

丸底フラスコに、Ｓｕｂ４（３５）（８．４ｇ、２０ｍｍｏｌ）、Ｓｕｂ５（７）（５．７ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、２−５８を１０．４ｇ（収率：８３％）得た。 2-58 Synthesis Example

Sub4 (35) (8.4 g, 20 mmol), Sub5 (7) (5.7 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) in a round bottom flask. ) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL), and then 10.4 g (yield) of 2-58 in the same manner as in the 2-34 synthesis method. Rate: 83%) Obtained.

丸底フラスコに、Ｓｕｂ４（３２）（１２．９ｇ、２０ｍｍｏｌ）、Ｓｕｂ５（１１）（７．９ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、２−５９を５．２ｇ（収率：７９％）得た。 2-59 Synthesis Example

Sub4 (32) (12.9 g, 20 mmol), Sub5 (11) (7.9 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) in a round bottom flask. ) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL), and then 5.2 g (yield) of 2-59 in the same manner as in the 2-34 synthesis method. Rate: 79%) Obtained.

丸底フラスコにＮ−（［１，１’−ビフェニル］−４−イル）−９，９−ジメチル−９Ｈ−フルオレン−２−アミン（７．２ｇ、２０ｍｍｏｌ）、４−（２−ブロモフェニル）−９，９−ジフェニル−９Ｈ−フルオレン（９．５ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、２−６９を１２．２ｇ得た（収率：８１％）。 2-69 Synthesis Example

N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluorene-2-amine (7.2 g, 20 mmol), 4- (2-bromophenyl) in a round bottom flask -9,9-diphenyl-9H-fluorene (9.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ (0.2 g, 2 mmol), t After adding −BuONa (5.8 g, 60 mmol) and toluene (300 mL), 12.2 g of 2-69 was obtained in the same manner as in the 2-34 synthesis method (yield: 81%).

丸底フラスコに、Ｎ−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）ジベンゾ［ｂ，ｄ］フラン−１−アミン（７．５ｇ、２０ｍｍｏｌ）、Ｎ−（３−ブロモフェニル）−N−（９，９−ジメチル−９Ｈ−フルオレン−２−イル）ジベンゾ［ｂ，ｄ］フラン−１−アミン（１０．６ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、２−７１を１２．９ｇ得た（収率：７８％）。 2-71 Synthesis Example

In a round bottom flask, N- (9,9-dimethyl-9H-fluorene-2-yl) dibenzo [b, d] furan-1-amine (7.5 g, 20 mmol), N- (3-bromophenyl)- N- (9,9-dimethyl-9H-fluorene-2-yl) dibenzo [b, d] furan-1-amine (10.6 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol) ), P (t-Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), and toluene (300 mL), and then 2-34 in the same manner as in the 2-34 synthesis method. 12.9 g of 71 was obtained (yield: 78%).

[Synthesis Example 4]
The compound (final product) represented by the formula (30) according to the present invention is produced by reacting Sub30 and Sub31 as in the following reaction scheme 5, but is not limited thereto.
<Reaction scheme 5>

Sub30 synthesis example <Reaction scheme 6>

丸底フラスコに、３−（９−フェニル−９Ｈ−フルオレン−９−イル）アニリン（６．７ｇ、２０ｍｍｏｌ）、２−ブロモ−９，９−ジメチル−９Ｈ−フルオレンe（５．５ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、Ｓｕｂ３０（８１）を８．８３ｇ（収率：８４％）得た。 Synthesis example of Sub30 (81)

In a round bottom flask, 3- (9-phenyl-9H-fluorene-9-yl) aniline (6.7 g, 20 mmol), 2-bromo-9,9-dimethyl-9H-fluorene e (5.5 g, 20 mmol) , Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) ₃ (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL). After that, 8.83 g (yield: 84%) of Sub30 (81) was obtained in the same manner as in the 2-34 synthesis method.

Examples of Sub31 Examples of Sub31 are as follows, but are not limited thereto.

丸底フラスコに、Ｎ−（３−（９−フェニル−９Ｈ−フルオレン−９−イル）フェニル）ジベンゾ［ｂ，ｄ］フラン−１−アミン（１０．０ｇ、２０ｍｍｏｌ）、２−ブロモ−９，９−ジメチル−９Ｈ−フルオレン（５．５ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後、前記２−３４合成方法と同様にして、２−７２を１１．１ｇ得た（収率：８０％）。 2-72 Synthesis Example

In a round bottom flask, N- (3- (9-phenyl-9H-fluorene-9-yl) phenyl) dibenzo [b, d] furan-1-amine (10.0 g, 20 mmol), 2-bromo-9, 9-Dimethyl-9H-fluorene (5.5 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) 3 (0.2 g, 2 mmol), t-BuONa ( After adding 5.8 g (60 mmol) and toluene (300 mL), 11.1 g of 2-72 was obtained in the same manner as in the 2-34 synthesis method (yield: 80%).

丸底フラスコに、Ｓｕｂ３０（８１）（１０．３ｇ、２０ｍｍｏｌ）、Ｓｕｂ３１−４（４．６６ｇ、２０ｍｍｏｌ）、Ｐｄ_２（ｄｂａ）_３（０．５ｇ、０．６ｍｍｏｌ）、Ｐ（ｔ−Ｂｕ）_３（０．２ｇ、２ｍｍｏｌ）、ｔ−ＢｕＯＮａ（５．８ｇ、６０ｍｍｏｌ）、トルエン（３００ｍＬ）を添加した後。前記２−３４合成方法と同様にして、２−８１を１０．３ｇ得た（収率：７６％）。 2-80 synthesis example

Sub30 (81) (10.3 g, 20 mmol), Sub31-4 (4.66 g, 20 mmol), Pd ₂ (dba) ₃ (0.5 g, 0.6 mmol), P (t-Bu) in a round bottom flask. _{After adding 3} (0.2 g, 2 mmol), t-BuONa (5.8 g, 60 mmol), toluene (300 mL). 10.3 g of 2-81 was obtained in the same manner as in the 2-34 synthesis method (yield: 76%).

Manufacturing Evaluation of Organic Electronic Devices Experimental Example 1) Manufacturing and testing of green organic light emitting devices (host)
First, on the ITO layer formed on a glass substrate (positive electrode), ^{N 1} as the hole injection layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - bis (4- (naphthalen-2-yl (phenyl ) Amino) phenyl) -N ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film was vacuum-deposited to form a thickness of 60 nm. Next, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as'-NPD') was vacuum-deposited on this membrane to a thickness of 60 nm as a hole transport compound. To form a hole transport layer. Then, the compound of the invention represented by the formula (1) was used as the host, and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] was doped as the dopant at a weight of 95: 5, so that the positive was positive. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') is vacuum-deposited to a thickness of 10 nm. , Tris (8-quinolinol) aluminum (hereinafter abbreviated as'Alq3') was formed to a thickness of 40 nm as an electron transport layer. Subsequently, LiF, which is an alkali metal halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the T95 life was measured with the life measurement equipment of McScience Co., Ltd. at ^{5000 cd / m 2 reference brightness.} The table below shows the results of device fabrication and evaluation.

[Comparative Examples 1 to 4]
An organic electron light emitting device was produced in the same manner as in Experimental Example 1 except that Comparative Compound A, Comparative Compound B, Comparative Compound C and Comparative Compound D were used as hosts.

Experimental Example 2) Manufacture and test of green organic light emitting device (mixed host)
ITO layer formed on the glass substrate over (positive), ^{N 1} is first as the hole injecting layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - bis (4- (naphthalen-2-yl (phenyl) Amino) phenyl) -N ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film was vacuum-deposited to form a thickness of 60 nm. Next, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as'-NPD') was vacuum-deposited on this membrane to a thickness of 60 nm as a hole transport compound. And formed a hole transport layer. After that, a mixture of the above-mentioned invention compounds represented by the formulas (1) and (12) was used as the host, and Ir (ppy) ₃ [tris (2-phenylpyridine) -iridium] was used as the dopant. A light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by doping with a weight of 5. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') was vacuum-deposited to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter _{abbreviated as'Alq 3} ') was formed as an electron transport layer to a thickness of 40 nm. Subsequently, LiF, which is an alkali metal halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the T95 life was measured with the life measurement equipment manufactured by McScience with a reference brightness of ^{5000 cd / m 2.} The table below shows the results of device fabrication and evaluation.

[Comparative Examples 5-8, 10-13]
Organic electron emission is carried out in the same manner as in Example 2 except that the comparative compound A, the comparative compound B, the comparative compound C, and the comparative compound D are used instead of the invention compound represented by the formula (1) as the host. I made the element.

[Comparative Examples 9, 14]
An organic electron light emitting device was produced in the same manner as in Experimental Example 2 except that the comparative compound E was used instead of the invention compound represented by the formula (12) as the host.

Experimental example 3) Manufacture and test of green organic light emitting device (light emitting auxiliary layer + mixed host)
On the ITO layer formed on a glass substrate (positive electrode), first, ^{N 1} as the hole injection layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - bis (4- (naphthalen-2-yl (phenyl ) Amino) phenyl) -N ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film was vacuum-deposited to form a thickness of 60 nm. Next, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as'-NPD') was vacuum-deposited on this membrane to a thickness of 60 nm as a hole transport compound. And formed a hole transport layer. Then, the compound of the invention represented by the formula (18) was vacuum-deposited to a thickness of 20 nm as a light emitting auxiliary layer material to form a light emitting auxiliary layer. After forming the light emitting auxiliary layer, a mixture of the above-mentioned invention compounds represented by the formulas (1) and (12) represented by the formulas (1) and (12) is used as a host on the upper part of the light emitting auxiliary layer, and Ir (ppy) ₃ [is used as a dopant. A 30 nm thick light emitting layer was deposited by doping Tris (2-phenylpyridine) -iridium] at a weight of 95: 5. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') was vacuum-deposited to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter _{abbreviated as'Alq 3} ') was formed as an electron transport layer to a thickness of 40 nm. Subsequently, LiF, which is an alkali metal halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the T95 life was measured with the life measurement equipment manufactured by McScience with a reference brightness of ^{5000 cd / m 2.} The table below shows the results of device fabrication and evaluation.

[Comparative Examples 15 to 29]
An organic electron light emitting device was produced by the same method as in Experimental Example 3 except that Comparative Compound A to Comparative Compound E were used instead of the invention compound represented by the formula (1) as a host.

Experimental Example 4) Manufacture and test of green organic light emitting device (hole transport layer + light emitting auxiliary layer + mixed host)
On the ITO layer formed on a glass substrate (positive electrode), ^{N 1} as the hole injection layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - bis (4- (naphthalen-2-yl (phenyl) amino ) Phenyl) -N ¹ -Phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film was vacuum-deposited to form a thickness of 60 nm. Next, the compound of the invention represented by the formula (18) as hole transport was vacuum-deposited on this film to a thickness of 60 nm to form a hole transport layer. Further, the compound of the invention represented by the formula (18) was vacuum-deposited to a thickness of 20 nm as a light emitting auxiliary layer material to form a light emitting auxiliary layer. After forming the light emitting auxiliary layer, a mixture of the above invention compound 6: 4 represented by the formulas (1) and (12) is used as a host on the upper part of the light emitting auxiliary layer, and Ir (ppy) ₃ [is used as a dopant. A 30 nm thick light emitting layer was deposited by doping Tris (2-phenylpyridine) -iridium] at a weight of 95: 5. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') was vacuum-deposited to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter abbreviated as'Alq3') was formed as an electron transport layer to a thickness of 40 nm. Subsequently, LiF, which is an alkali metal halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the T95 life was measured with the life measurement equipment manufactured by McScience with a reference brightness of ^{5000 cd / m 2.} The table below shows the results of device fabrication and evaluation.

As can be seen from the results in Tables 7 to 10, the organic electron light emitting device using the material for the organic electron light emitting device of the present invention as a phosphorescent host significantly improves high luminous efficiency, low drive voltage, and life. I was able to.

Table 7 describes the excellence of the invention compound represented by the formula (1) as compared with the comparative compound when it is used as a single host. From the results of Comparative Compound A and Comparative Compound C, it was confirmed that the performance was improved in all aspects of drive, efficiency and lifetime when 3-dibenzofuran was substituted rather than 4-dibenzofuran. From the results of Comparative Compound A and Comparative Compound B, or Comparative Compound C and Comparative Compound D, it was found that the performance is improved by substituting two dibenzothiophene or dibenzofuran moieties with triazine. I was able to confirm. Therefore, the invention compound in which triazine is substituted with 3-dibenzofuran and 4-dibenzothiophene having a linking group on the other side is always substituted has improved results that are significantly different from those of Comparative Compounds A to D. I was finally able to confirm that it was shown. This is because the energy level of the compound (HOMO, LUMO, T1, etc.) changes remarkably depending on the type or substitution position of the substituent, and the difference in the physical properties of such a compound is a major factor in improving the device performance during device deposition. It acts as an energy balance (for example), suggesting that such different device results may be derived.

Table 8 explains that when the compound represented by the formula (12) and the compound of the formula (1) are mixed, they are significantly superior to other comparative combinations. As a result, it also supports the contents explained in the case of a single host, and when combined with equation (12), the drive and efficiency are improved by about 24% and the life is further improved by about 63% compared to the case of a single host. It was confirmed that there is a possibility. When two hosts are premixed and used, the aging rate is very important for vapor deposition at a predetermined ratio, and the compound of the present invention has an excellent aging rate as compared with other materials. In particular, compounds in which at least one of ^{Ar 1} , Ar ³ , and R ³ _{is an aryl group of C 6 to} C ₂₄ showed the best results in the time-lapse test.

Table 9 shows an example in which a mixed compound of the formula (1) and the formula (12) was used as the light emitting layer host, and the compound represented by the formula (18) was used as the light emitting auxiliary layer, and the efficiency was higher than that of Table 8. Shows a result that the life is improved by about 60% and the life is improved by about 20%. When the hole transport layer compound was also a compound represented by the formula (18), a result was obtained in which the drive voltage, efficiency, and life were slightly improved from the results in Table 7 above.

That is, the compound of the present invention represented by the formula (1) showed further improved results as compared with the already known similar substances even when used as a single host, but is shown by the formula (12). Remarkably excellent results were obtained when the light emitting auxiliary layer or the hole transporting layer was used in combination with the compound represented by the formula (18).

Experimental Example 5) onto the blue organic ITO layer manufactured and formed in the test glass substrate of the light emitting element (positive electrode), first, ^{N 1} as the hole injection layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - A bis (4- (naphthalene-2-yl (phenyl) amino) phenyl) -N- ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film is vacuum-deposited to a thickness of 60 nm. Formed in. Next, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as'-NPB') was vacuum-deposited on this membrane to a thickness of 60 nm as a hole transport compound. And formed a hole transport layer. Then, the compound of the present invention was vacuum-deposited to a thickness of 20 nm as a light emitting auxiliary layer material to form a light emitting auxiliary layer. After forming the light emitting auxiliary layer, 9,10-di (naphthalene-2-yl) anthracene as a host and BD-052X (manufactured by Idemitsu Kosan Co., Ltd.) as a dopant are placed on the upper part of the light emitting auxiliary layer at a weight of 96: 4. By doping, a light emitting layer having a thickness of 30 nm was deposited on the light emitting auxiliary layer. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') was vacuum-deposited to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter abbreviated as'Alq3') was formed as an electron transport layer to a thickness of 40 nm. Subsequently, LiF, which is an alkali metal halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the T95 life was measured with the life measurement equipment manufactured by McScience with a reference brightness of ^{500 cd / m 2.} The table below shows the results of device fabrication and evaluation.

[Comparative Examples 35 to 37]
An organic electron light emitting device was produced in the same manner as in Comparative Experimental Example 5 except that Comparative Compound F, Comparative Compound G, and Invented Compound 2-81 were used as the hole transport layer material without using the light emitting auxiliary layer. ..

[Comparative Example 38]
An organic electron light emitting device was manufactured by the same method as in Comparative Experimental Example 5 except that the light emitting auxiliary layer was not used.

[Comparative Example 39 to Comparative Example 40]
An organic electron light emitting device was produced in the same manner as in Comparative Experimental Example 5 except that Comparative Compound F or Comparative Compound G was used as the light emitting auxiliary layer material.

On Experimental Example 6) Green organic ITO layer manufactured and formed in the test glass substrate of the light emitting element (positive electrode), first, ^{N 1} as the hole injection layer - ^{(naphthalen-2-yl)} -N 4, ^{N 4} - A bis (4- (naphthalene-2-yl (phenyl) amino) phenyl) -N- ¹ -phenylbenzene-1,4-diamine (hereinafter abbreviated as '2-TNATA') film is vacuum-deposited to a thickness of 60 nm. Formed in. Next, 4,4-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as'-NPD') was vacuum-deposited on this membrane to a thickness of 60 nm as a hole transport compound. Then, an m-hole transport layer was formed. Then, the compound of the invention represented by the formula (30) was vacuum-deposited to a thickness of 20 nm as a light emitting auxiliary layer material to form a light emitting auxiliary layer. After forming the luminescence auxiliary layer, 4,4'-di (9H-carbazole-9-yl) -1,1'-biphenyl is used as a host on the upper part of the luminescence auxiliary layer, and Ir (ppy) 3 is used as a dopant. A 30 nm thick light emitting layer was deposited by doping [Tris (2-phenylpyridine) -iridium] at a weight of 95: 5. As the hole element layer, (1,1'-bisphenyl) -4-oleate) bis (2-methyl-8-quinoline oleate) aluminum (hereinafter abbreviated as'BAlq') was vacuum-deposited to a thickness of 10 nm. Tris (8-quinolinol) aluminum (hereinafter abbreviated as'Alq3') was formed as an electron transport layer to a thickness of 40 nm. Subsequently, LiF, which is an alkali metal h halide, was vapor-deposited to a thickness of 0.2 nm as an electron injection layer, and then Al was vapor-deposited to a thickness of 150 nm, and used as a negative electrode to manufacture an organic electroluminescent element.

A forward bias DC voltage was applied to the organic electron light emitting devices of Examples and Comparative Examples manufactured in this manner, and the electric light emission (EL) characteristics were measured with PR-650 manufactured by PhotoResearch. As a result of the measurement, the life of dT95, a life measuring device manufactured by McScience, was measured at ^{5000 cd / m 2 reference brightness.} The table below shows the results of device fabrication and evaluation.

[Comparative Examples 41 to 42]
An organic electron light emitting device was produced in the same manner as in Comparative Experimental Example 5 except that Comparative Compound F or Comparative Compound G was used as the light emitting auxiliary layer material.

As can be seen from the results in Tables 11 to 12, when an organic electron light emitting element is manufactured using the material for an organic electron light emitting element of the present invention as a light emitting auxiliary layer material, it is compared whether or not it is used as a material for a light emitting auxiliary layer. It was found that not only the driving voltage of the organic electron light emitting element can be lowered as compared with the comparative example using the compound F or the comparative compound G, but also the luminous efficiency and the life can be remarkably improved.

Table 11 shows the results of producing a blue organic light emitting device, and it was confirmed that excellent results can be obtained when the compound of the present invention is used as a light emitting auxiliary layer. From the results of Comparative Example 39 or Comparative Example 40 and Examples 57 to 70, the specific substituents such as DBT, DBF, Cz, and fluorene were different from the comparative compounds in which the general aryl groups were substituted even though the mother nuclei were similar. It was confirmed that the compound of the present invention in which is substituted is remarkably excellent. This is because when a specific substituent such as DBT, DBF, Cz, or fluorene is introduced, the refractive index, Tg, and the energy level of the compound (HOMO, LUMO, T1, etc.) change significantly, and such physical characteristics It is suggested that the difference between the above acts as a major factor (for example, energy balance) in improving the element performance during element deposition, and such a difference element result may be derived.

Table 12 shows the results of producing a green organic light emitting device, and it was confirmed that when the compound of the present invention was used as a light emitting auxiliary layer, it was remarkably superior to the comparative compound. This is also the effect of specific substituents such as DBT, DBF, Cz, and fluorene, but it is confirmed that the superior degree is significantly improved in the case of the green auxiliary layer rather than the blue auxiliary layer. did it. Furthermore, in the case of the blue auxiliary layer, the compound in which DBT and DBF were substituted showed the best characteristics, but in the result of the green auxiliary layer, the compound in which fluorene was substituted showed the best result. Even with such a light emitting auxiliary layer compound, the required characteristics change depending on the color of the light emitting layer, suggesting that a result that cannot be inferred by those skilled in the art may be derived.

The above description is merely an exemplary description of the present invention. A person having ordinary knowledge in the technical field belonging to the present invention can make various modifications within a range that does not deviate from the essential characteristics of the present invention. Therefore, the examples disclosed in the present specification are not for limiting the present invention, but for explaining the present invention, and such examples do not limit the idea and scope of the present invention. The scope of protection of the present invention should be construed by the following claims, and within the equivalent scope, all techniques should be construed as being included in the scope of rights of the present invention.

100: Organic electronic device 110: Substrate 120: First electrode (positive electrode)
130: Hole injection layer 140: Hole transport layer 141: Buffer layer 150: Light emitting layer 151: Light emitting auxiliary layer 160: Electron transport layer 170: Electron injection layer 180: Second electrode (negative electrode)

［式（１）及び式（１８）中、
１）Ａｒ^１、Ａｒ^２、Ａｒ^３、ｌ、ｍ、ｎ、ａ、ｂ、ｃ、ｄ、ｅ、ｎ、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４及びＲ^５は、請求項１に記載の定義と同義であり、
２）Ａｒ^４及びＡｒ^５は、お互い独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）｛ここで、Ｌ’は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、Ｒ_ａ及びＲ_ｂは、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、又はＡｒ^４とＡｒ^５が、互いに結合して、環を形成していてもよい｝；からなる群から選ばれ、
３）Ａｒ^６は、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれるか、又は下記式（１−a）、（１−b）、（１−c）の少なくとも一つであり、

４）Ａｒ^９〜Ａｒ^１１は、互いに独立して、Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）；からなる群から選ばれ、
５）ｈ、ｉ及びｇは、０〜４の整数であり；ｊは、０〜３の整数であり；Ｒ^６〜Ｒ^９は、同じであるか又は異なり、互いに独立して、水素；重水素；ハロゲン；Ｃ_６〜Ｃ_６０のアリール基；フルオレニル基；Ｏ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；Ｃ_１〜Ｃ_５０のアルキル基；Ｃ_２〜Ｃ_２０のアルケニル基；Ｃ_２〜Ｃ_２０のアルキニル基；Ｃ_１〜Ｃ_３０のアルコキシル基；Ｃ_６〜Ｃ_３０のアリールオキシ基；及び−Ｌ’−Ｎ（Ｒ_ａ）（Ｒ_ｂ）；からなる群から選ばれ、
又は、Ｒ^６〜Ｒ^９は、ｇ、ｈ、ｉ、ｊが２以上のとき、それぞれ複数として、互いに同じであるか又は異なり、互いに結合して、環を形成し、
６）Ｌ^６は、単結合；Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環の縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれ、
７）Ｌ^５は、Ｃ_６〜Ｃ_６０のアリーレン基；フルオレニレン基；Ｃ_３〜Ｃ_６０の脂肪族環とＣ_６〜Ｃ_６０の芳香族環との縮合環基；及びＯ、Ｎ、Ｓ、Ｓｉ及びＰの少なくとも一つのヘテロ原子を含むＣ_２〜Ｃ_６０のヘテロ環基；からなる群から選ばれる。］ In another example, the present invention is an organic electronic element including a positive electrode; a negative electrode; and an organic substance layer formed between the positive electrode and the negative electrode; the organic substance layer includes a light emitting layer, and the positive electrode and the light emitting layer. The hole transport layer or the light emission auxiliary layer is a compound represented by the following formula (18), including a hole transport layer formed between the light emitting layer and a light emitting auxiliary layer formed between the light emitting layer and the hole transport layer. The light emitting layer provides an organic electronic element containing the compound represented by the following formula (1).

[In equations (1) and (18),
1) Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are described in claim 1. Is synonymous with the definition of
2) Ar ⁴ and Ar ⁵ are independent of each other and are C _{6 to} C _{60 aryl groups; fluorenyl groups; C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C _{2 to} C ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b ) {where L'is a single bond; C A group consisting of an arylene group of _{6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and a hetero ring group of _{C 2 to} C _60; is selected from, _{R a} and _{R b} are, independently of one _another, an aryl group of C 6 _{-C 60;} condensation of aromatic ring of C 3 aliphatic ring and _C 6 _{-C 60} of _{-C 60;} fluorenyl group Selected from the group consisting of ring groups; and _{C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P ^{; or Ar 4} and Ar ⁵ bonded to each other. , May form a ring}; selected from the group consisting of
3) Ar ⁶ is selected from the group consisting of _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a heterocyclic group of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Or at least one of the following formulas (1-a), (1-b), (1-c),

4) Ar ^{9 to} Ar ¹¹ are independent of each other, _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a hetero of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C ₂ to C 20 Selected from the group consisting of ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b);
5) h, i and g are integers from 0 to 4; j is an integer from 0 to 3; R ^{6 to} R ⁹ are the same or different, independent of each other, hydrogen; heavy. Hydrogen; Halogen; _{Aryl group of C 6 to} C ₆₀ ; Fluolenyl group; Hetero ring group of _{C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Fat of _{C 3 to} C ₆₀ alkynyl group _C 2 ~C _20;; alkenyl C 2 _{-C 20;} alkyl radical of C 1 _{-C 50;} fused ring group of the aromatic ring of the group ring and _C 6 _{~C 60 C} 1 _{~C 30} Alkyloxy groups of C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b );
Alternatively, ^{when g, h, i, and j are 2 or more, R 6 to} R ⁹ are the same or different from each other as a plurality, and are combined with each other to form a ring.
6) L ⁶ is a single bond; _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, Selected from the group consisting of _{C 2 to} C ₆₀ heterocyclic groups containing at least one heteroatom of S, Si and P;
7) L ⁵ is _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, S, heterocyclic group _C 2 _{-C 60} containing at least one heteroatom Si and P; selected from the group consisting of. ]

Claims (34)

Compound represented by the following formula (1):

[In the formula, 1) Ar ¹ , Ar ² and Ar ³ are aryl groups of _{C 6 to} C ₆₀ independently of each other.
2) l + e is an integer of 0 to 4, d + m is an integer of 0 to 4, a and b are integers of 0 to 3, n is an integer of 1 to 3, and c is an integer of 0 to 4.
3) R ¹ , R ² , R ³ , R ⁴ and R ⁵ are independent of each other, hydrogen; heavy hydrogen; halogen; _{aryl groups of C 6 to} C ₆₀ ; fluorenyl groups; O, N, S, Si and fused ring group with a C 3 _{-C 60} aliphatic ring and _C 6 _{-C 60} aromatic _ring;; P of _C 2 _{-C 60} heterocyclic group containing at least one hetero atom C 1 _{-C 50} of an aryloxy group having C 6 _{-C 30;;} alkyl _group; a C 2 _{-C 20} alkynyl _group;; C 2 _{-C 20} alkenyl group C 1 _{-C 30} alkoxyl group and -L'-N _(R a) _(R b) {wherein, L 'represents a single _bond; fused ring with C 3 aliphatic ring and _C 6 _{-C 60} of _{-C 60} aromatic _ring; C for 6 _{-C 60} arylene group; fluorenylene group selected from the group consisting of, _{R a} and _{R b} are, independently of one _another, a C 6 _{-C 60} aryl group; a heterocyclic group and _C 2 _{-C 60;} group C 3 _{-C 60;} fluorenyl group A group consisting of a fused ring group of an aliphatic ring and an aromatic ring of C _{6 to} C ₆₀ ; and a hetero ring group of _{C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; chosen} from; is selected from the group consisting of, or a plurality of ^{R 1} each other, a plurality of ^{R 2} to each other, a plurality of ^{R 3} to each other, a plurality of ^{R 4} with each other, a plurality of ^{R 5} each other, bonded to each other, It may form aromatic and heteroaromatic rings,
The aryl group, fluorenyl group, arylene group, heterocyclic group, fluorenylene group, fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxy group are each heavy hydrogen; halogen; silane group; siloxane group; boron group; germanium. Groups; Cyano groups; Nitro groups; C _1- C ₂₀ alkylthio groups; C _1- C ₂₀ alkoxyl groups; C _1- C ₂₀ alkyl groups; C _2- C ₂₀ alkenyl groups; C _2- C ₂₀ cycloalkyl groups C 3 _{-C 20;} heterocyclic group of C 2 _{-C 20;} alkynyl _group; C 6 _{-C 20} aryl group; a _C 6 _{-C 20} substituted with deuterium aryl group; a fluorenyl group; It may be further substituted with one or more substituents selected from the group consisting of _{C 7-} C ₂₀ arylalkyl groups and C _8- C _{20 arylalkenyl groups; and these substituents may be.} , They may be combined with each other to form a ring, where the "ring" is an aliphatic ring of _{C 3-} C ₆₀ or an aromatic ring of _{C 6-} C ₆₀ or a hetero of _{C 2-} C _60. It means a fused ring composed of a ring or a combination thereof, and includes a saturated or unsaturated ring. ] The compound according to claim 1, wherein the compound represented by the formula (1) is represented by any one of the following formulas (2) to (7):

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are claimed in claim 1. It is synonymous with the definition described in.) The compound according to claim 1, wherein at least one ^{of Ar 1} , Ar ³ and R ³ of the formula (1) is _{an aryl group of C 6 to} C _24. The compound according to claim 1, ^{wherein Ar 1} or Ar ³ of the formula (1) is _{an aryl group of C 6 to} C _24. The compound according to claim 1, ^{wherein R 3 of the} formula (1) is _{an aryl group of C 6 to} C _24. The compound according to claim 1, wherein the formula (1) is represented by any one of the following formulas (8) to (10).

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ , R ⁵ claim 1 It is synonymous with the definition described in.) The compound according to claim 1, wherein the compound represented by the formula (1) is represented by the following formula (11):

(In the formula, Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ , R ⁵ claim 1 It is synonymous with the definition described in.) In the first term, the compound represented by the formula (1) is a compound represented by any one of the following compounds:

An organic electronic device including a first electrode; a second electrode; and an organic substance layer formed between the first electrode and the second electrode and containing the compound according to any one of claims 1 to 4. .. The organic substance layer includes at least one layer of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer.
At least one of the hole injection layer, the hole transport layer, the light emitting auxiliary layer, the light emitting layer, the electron transport auxiliary layer, the electron transport layer and the electron injection layer is one of the compounds according to claim 1 alone or 2 The organic electronic element according to claim 9, wherein the organic electronic element contains more than one species. The organic electronic device according to claim 10, wherein the compound is contained in the light emitting layer. The organic electronic device according to claim 11, wherein the light emitting layer further contains at least one compound represented by the following formula (12).

[In the formula, 1) Z ^{1 to} Z ¹⁶ are independently CR or N (where R is hydrogen, _{an aryl group of C 6 to} C ₆₀ ; at least of O, N, S, Si and P). Selected from the group consisting of a heterocyclic group of _{C 3 to} C ₆₀ containing one heteroatom; an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C ₆₀ ; a fluorene group; and bonded to an adjacent group. To form a ring)
2) L ² is a group selected from the group consisting of a single bond; an arylene group of _{C 6 to} C _{60 ; a heteroarylene group of C 3 to} C ₆₀ ; and a divalent aliphatic hydrocarbon group;
3) W is ^{NAr 5} , O, S or CR'R'' (where R'and R'' are independently alkyl groups of _{C 1 to} C ₅₀ ; aryls of _{C 6 to} C _{60. Groups; or C 3 to} C ₆₀ heterocyclic groups containing at least one heteroatom of O, N, S, Si, P, which may be attached to each other to form a spiro compound). And
4) Ar ⁴ and Ar ⁵ are independent _{aryl groups of C 6 to} C ₆₀ ; heterocyclic groups of _{C 3 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; It is selected from the group consisting of an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C _{60; a fluorene group;} ] The organic electronic device according to claim 12, wherein the formula (12) is represented by any one of the following formulas (13) to (16).

(In the formula, Ar ⁴ , Ar ⁵ , Z ^{1 to} Z ¹⁶ , L2, R', R'' are synonymous with the definition described in claim 12.) The organic electronic device according to claim 12, ^{wherein Ar 4} and Ar ⁵ of the above formula (12) are all represented _{by aryl groups of C 6 to} C _30. The organic electronic device according to claim 12, wherein the compound represented by the formula (12) is represented by the following formula (17):

[In the formula, Ar ⁴ , Ar ⁵ , Z ^{1 to} Z ¹⁶ , L ² have the same meaning as the definition described in claim 12.
1) L ¹ is selected from the group consisting of a single bond; an arylene group of _{C 6 to} C _{60 ; a heteroarylene group of C 3 to} C ₆₀ ; and a divalent aliphatic hydrocarbon group;
2) Y is O, S or NAr ⁵ and
3) R ^a and R _b contain at least one heteroatom of hydrogen; heavy hydrogen; halogen; _{aryl group of C 6 to} C ₆₀ ; fluorenyl group; O, N, S, Si and P independently of each other. of _{C 2 ~C 20; C 2 ~C} 60 heterocyclic _group, alkyl group of _{C 1 ~C 50; C 3 ~C} 60 fused ring group and an aromatic ring of the aliphatic ring and _C 6 _{-C 60} Alkenyl groups; alkynyl groups of _{C 2 to} C ₂₀ ; alkoxyl groups of _{C 1 to} C _{30 ; aryloxy groups of C 6 to} C ₃₀ ; and -L'-N ( _Ra ) (R _b ) {where L 'Is a single bond; _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C _{60 ; and C 2 to} C ⁶⁰ . Selected from the group consisting of heterocyclic groups; _Ra and R _b are independent of each other, aryl groups of _{C 6 to} C ₆₀ ; fluorenyl groups; aliphatic rings of _{C 3 to} C _{60 and C 6 to} C _{60. Selected from the group consisting of fused ring groups with aromatic rings; and C 2 to} C ₆₀ hetero ring groups containing at least one heteroatom of O, N, S, Si and P; or a plurality of R ^1s. each other, a plurality of R ² to each other, a plurality of R ³ to each other, a plurality of R ⁴ with each other, a plurality of R ⁵ together are linked to each other, an aromatic and may also} to form a heteroaromatic ring; the group consisting of It may be selected from, or a plurality of Ras and ^a plurality of R ^bs may be bonded to each other to form an aromatic and a heteroaromatic ring.
4) y is an integer of 0 to 3, and z is an integer of 0 to 4. ] The organic electronic device according to claim 12, wherein the compound represented by the formula (12) is a compound represented by any one of the following compounds:

A positive electrode; a negative electrode; and an organic electronic device including an organic substance layer formed between the positive electrode and the negative electrode.
The organic substance layer includes a light emitting layer and includes a hole transport layer formed between the positive electrode and the light emitting layer; a light emitting auxiliary layer formed between the positive electrode and the hole transport layer; The light emitting auxiliary layer contains a compound represented by the following formula (18), and the light emitting layer contains a compound represented by the following formula (1).

[In equations (1) and (18),
1) Ar ¹ , Ar ² , Ar ³ , l, m, n, a, b, c, d, e, n, R ¹ , R ² , R ³ , R ⁴ and R ⁵ are described in claim 1. Is synonymous with the definition of
2) Ar ⁴ and Ar ⁵ are independent of each other and are C _{6 to} C _{60 aryl groups; fluorenyl groups; C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C _{2 to} C ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b ) {where L'is a single bond; C A group consisting of an arylene group of _{6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and a hetero ring group of _{C 2 to} C _60; is selected from, _{R a} and _{R b} are, independently of one _another, an aryl group of C 6 _{-C 60;} condensation of aromatic ring of C 3 aliphatic ring and _C 6 _{-C 60} of _{-C 60;} fluorenyl group Selected from the group consisting of ring groups; and _{C 2 to} C ₆₀ heteroatoms containing at least one heteroatom of O, N, S, Si and P ^{; or Ar 4} and Ar ⁵ bonded to each other. , May form a ring}; selected from the group consisting of
3) Ar ⁶ is selected from the group consisting of _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a heterocyclic group of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Or at least one of the following formulas (1-a), (1-b), (1-c),

4) Ar ^{9 to} Ar ¹¹ are independent of each other, _{an aryl group of C 6 to} C _{60 ; a fluorenyl group; a hetero of C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P. Ring groups; fused ring groups of C _{3 to} C ₆₀ aliphatic rings and C _{6 to} C _{60 aromatic rings; C 1 to} C ₅₀ alkyl groups; C _{2 to} C ₂₀ alkenyl groups; C ₂ to C 20 Selected from the group consisting of ₂₀ alkynyl groups; C _{1 to} C ₃₀ alkoxyl groups; C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b);
5) h, i and g are integers from 0 to 4; j is an integer from 0 to 3; R ^{6 to} R ⁹ are the same or different, independent of each other, hydrogen; heavy. Hydrogen; Halogen; _{Aryl group of C 6 to} C ₆₀ ; Fluolenyl group; Hetero ring group of _{C 2 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; Fat of _{C 3 to} C ₆₀ alkynyl group _C 2 ~C _20;; alkenyl C 2 _{-C 20;} alkyl radical of C 1 _{-C 50;} fused ring group of the aromatic ring of the group ring and _C 6 _{~C 60 C} 1 _{~C 30} Alkyloxy groups of C _{6 to} C ₃₀ aryloxy groups; and -L'-N ( _Ra ) (R _b );
Alternatively, ^{when g, h, i, and j are 2 or more, R 6 to} R ⁹ are the same or different from each other as a plurality, and are combined with each other to form a ring.
6) L ⁶ is a single bond; _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, Selected from the group consisting of _{C 2 to} C ₆₀ heterocyclic groups containing at least one heteroatom of S, Si and P;
7) L ⁵ is _{an arylene group of C 6 to} C ₆₀ ; a fluorenylene group; a fused ring group of an aliphatic ring of _{C 3 to} C _{60 and an aromatic ring of C 6 to} C ₆₀ ; and O, N, S, heterocyclic group _C 2 _{-C 60} containing at least one heteroatom Si and P; selected from the group consisting of. ] The organic electronic device according to claim 17, wherein the light emitting layer further contains at least one compound represented by the following formula (12).

[In the formula, 1) Z ^{1 to} Z ¹⁶ are independently CR or N (where R is hydrogen, _{an aryl group of C 6 to} C ₆₀ ; at least of O, N, S, Si and P). Selected from the group consisting of a heterocyclic group of _{C 3 to} C ₆₀ containing one heteroatom; an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C ₆₀ ; a fluorene group; and bonded to an adjacent group. To form a ring)
2) L ² is a group selected from the group consisting of a single bond; an arylene group of _{C 6 to} C _{60 ; a heteroarylene group of C 3 to} C ₆₀ ; and a divalent aliphatic hydrocarbon group;
3) W is ^{NAr 5} , O, S or CR'R'' (where R'and R'' are independently alkyl groups of _{C 1 to} C ₅₀ ; aryls of _{C 6 to} C _{60. Groups; or C 3 to} C ₆₀ heterocyclic groups containing at least one heteroatom of O, N, S, Si, P, which may be attached to each other to form a spiro compound). And
4) Ar ⁴ and Ar ⁵ are independent _{aryl groups of C 6 to} C ₆₀ ; heterocyclic groups of _{C 3 to} C ₆₀ containing at least one hetero atom of O, N, S, Si and P; It is selected from the group consisting of an alkyl group of _{C 1 to} C _{50 ; an arylamine group of C 6 to} C _{60; a fluorene group;} ] The organic according to claim 17, wherein the hole transport layer contains a compound represented by the following formula (19) or (20), and the light emitting auxiliary layer contains a compound represented by the following formula (21) or (22). Electronic element:

Wherein, 1) Ar ^{6 _'is} an aryl group of C 6 _{-C 60;} heterocyclic group _C 2 _{-C 60} containing O, N, S, at least one of the heteroatoms Si and P; fluorenyl group; Selected from a group of
2) Ar ⁴ , Ar ⁵ , Ar ^{9 to} Ar ¹¹ , h, i, g, L ⁵ , L ⁶ , and R ^{6 to} R ⁹ are synonymous with the definition described in claim 17. ] The organic electronic device according to claim 17, wherein the compound represented by the formula (18) is a compound represented by any one of the following compounds:

The organic electron according to claim 17, wherein the compounds represented by the formulas (1) and (18) are mixed at any one ratio of 1: 9 to 9: 1 and used for a light emitting layer. element. The organic electronic device according to claim 17, wherein the compound represented by the formula (1) is used as a phosphorescent host substance in the light emitting layer. The organic electronic device according to claim 17, further comprising a light efficiency improving layer formed on at least one surface opposite to the organic substance layer in one surface of the first electrode and the second electrode. The organic electronic element according to claim 17, wherein the organic material layer is formed by a spin coating step, a nozzle printing step, an inkjet printing step, a slot coating step, a dip coating step, or a roll-to-roll step. A positive electrode; a negative electrode; and an organic electronic device including an organic substance layer formed between the positive electrode and the negative electrode.
The organic layer includes a light emitting layer, includes a hole transport layer formed between the positive electrode and the light emitting layer, and a light emitting auxiliary layer or an electron blocking layer (EBL) formed between the positive electrode and the hole transport layer. An organic electronic element in which the light emitting auxiliary layer or the electron blocking layer contains a compound represented by the following formula (30):

[In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ and R ²⁵ are independent of each other: hydrogen; heavy hydrogen; halogen; _{aryl groups of C 6 to} C ₃₀ ; fluorenyl groups; O, N. , S, Si and P heteroatoms of C _{2 to} C ₃₀ containing at least one heteroatom; fused ring groups of C _{3 to} C ₃₀ aliphatic rings and C _{6 to} C ₃₀ aromatic rings; C from the group consisting of; and aryloxy groups of _{C 6 ~C 30; C 1 ~C} 30 alkoxy _group; C 2 _{-C 20} alkynyl _group; C 2 _{-C 20} alkenyl _{group; 1} -C ₃₀ alkyl group chosen, or a plurality of ^{R 20} each other between a plurality of ^{R 22,} together a plurality of ^{R 23,} a plurality of ^{R 24} to each other, a plurality of ^{R 25} each other, bonded to each other to form an aromatic or heteroaromatic ring May be
v is an integer of any one of 0 to 3.
u, w, x and y are independently integers of any one of 0 to 4.
Z is an integer of any one of 0 to 5,
L ²⁰ and L ²¹ are independently single bonds; C _{6 to} C ₃₀ arylene groups; C _{3 to} C ₃₀ heteroarylene groups;
Ar ²⁰ is _{an aryl group of C 6 to} C ₃₀ ; or a heteroarylene group of C _{3 to} C ₃₀ ;
X ²⁰ is O, S, NR'or CR'R'' {where R'and R'' are independently alkyl groups of _{C 1 to} C ₃₀ ; aryl groups of _{C 6 to} C _30. ; or O, N, S, Si, heterocyclic group of C ₃ -C 3 ₀ containing at least one heteroatom P; is, they may be bonded to each other to form a spiro compound }. ] The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is represented by any one of the following formulas (31) to (33):

(In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , L ²⁰ , L ²¹ , Ar ²⁰ and X ²⁰ , u, v, w, x, y and z are claims 25. It is synonymous with the definition described in.) The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is represented by any one of the following formulas (34) to (37):

(In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , L ²⁰ , L ²¹ , Ar ²⁰ and X ²⁰ , u, v, w, x, y and z are claims. It is synonymous with the definition described in 25.) The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is represented by the following formula (38):

(In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , L ²⁰ , L ²¹ , Ar ²⁰ and X ²⁰ , u, v, w, x, y and z are claims 25. It is synonymous with the definition described in.) The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is represented by the following formula (39) or (40):

(In the formula, R ²⁰ , R ²¹ , R ²² , R ²³ , R ²⁴ , R ²⁵ , L ²⁰ , L ²¹ , Ar ²⁰ and X ²⁰ , u, v, w, x, y and z are claims 25. It is synonymous with the definition described in.) The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is represented by any one of the following compounds:

The organic electronic device according to claim 25, wherein the compound represented by the formula (30) is used as a green light emitting auxiliary layer substance. The organic electronic device according to claim 29, wherein the compound represented by the formula (39) or (40) is used as a green light emitting auxiliary layer substance. A display device including the organic electronic device according to claim 9, 17 or 25; and a control unit for driving the display device;
Electronic devices including. 33. The electronic device according to claim 33, wherein the organic electronic device is at least one of an organic electron light emitting device, an organic solar cell, an organic photoconductor, an organic transistor, and a monochromatic or white illumination element.

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